The Long Con
by fadingtales
Summary: All it takes a little misguided hope, expertly placed, to bring down an empire. It’s what Jack Bass does best. WARNING! Spoilers for the upcoming episodes that haven't aired yet! Based on the latest spoilers for S3, takes place after 3x12. C/B Jack.
1. Chapter 1

**Title:** The Long Con  
**Author:** fading_tales  
**Pairing:** Chuck/Blair, Jack  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Summary:** All it takes a little misguided hope, expertly placed, to bring down an empire. It's what Jack Bass does best. In response to spoilers for S3, takes place after 3x12.

**I.**

The day Jack Bass returns to New York was an ordinary Monday. He gets off the private jet, nicely tanned from the Australian sun accompanied with a sort of diabolical twinkle in his eye. At least that's how he looks in the gossip girl photo blast. Blair is scanning through the various articles about the senior Bass's return from the down under when speak of the devil… As unnerving it was to look at the mere picture of Jack Bass on the small phone screen, it was even more unnerving facing him in person. The digital image she was just looking at is replaced by Jack in the flesh, that evil glint in his eye as evident as it was in the photo.

"Blair, how nice it is to see you again. I really did miss our encounters."

"What are you doing here, Jack? Last time I heard you were banished and in exile. What could have possibly brought you out of your little hidey hole?"

"The memory of your legs wrapped around my waist."

There was no doubt about the family resemblance. Uncle and nephew both had an inclination towards some infamous Bass debauchery.

"Chuck's not going to stand for this. He'll have you on the next plane back to the land of koalas and kangaroos, tail tucked between your legs before you can set your suitcase down."

"I really did miss that mouth of yours," Jack says with an unwavering smile. "You tell Chuckie boy that I'm back and I'm not going anywhere. As for you…" his gaze drops, taking in her figure and Blair subconsciously crosses her arms feeling violated, "we'll be seeing more of each other soon enough."

"Over my dead body."

"I'm game for all sorts of things, but necrophilia isn't one of them… but maybe for you I can make an exception."

At this point Blair's too disgusted to even come up with a reply.

"Come now, Blair. I know you had a good time…" he says reaching for her hand. She quickly pulls her hand out of range.

"Spare me the overcompensating antics that do nothing to cover up your older brother-complex. We've been there, done that. Now we're just done. Please pack your little insecurities and diabolical plans back in that tacky Louis Vuitton suitcase and hit the road now when I'm still asking nicely."

"You know me, Blair. I always liked you better when you didn't play nice," he says reaching to stroke her cheek, but she slaps it away. He laughs in response. "I'll see you later."

He gives her a blindingly white smile that speaks of horrors to come and walks out the door as easily as he strolled in. Blair officially hates Mondays.

---

**A/N**: I hope you guys liked it! I'm planning this to be a bit of a "mini" multi-chapter series. Meaning there's going to be a few more installments, but they'll be in the form of short parts rather than whole chapters. Reviews are love! 3 Let me know what you think and whether or not I should continue!


	2. Chapter 2

**Title:** The Long Con  
**Author:** fading_tales  
**Pairing:** Chuck/Blair, Jack  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Spoilers:** WARNING! Spoilers for the upcoming episodes that haven't aired yet!  
**Summary:** All it takes a little misguided hope, expertly placed, to bring down an empire. It's what Jack Bass does best. Based on the latest spoilers for S3, takes place after 3x12 (The Debarted).

**II.**

True to his word, Jack Bass turns the Upper East Side on its head. Jack had not come back to New York alone. His arrival brings a shocking, head-spinning reveal about Chuck's birth. The revelation is as simple as it is devastating.

His mother is alive.

Evelyn Bass who's been absent all of Chuck's life, the reason for his estrangement with the late Bart Bass, is in fact alive and in their very city. The knowledge of her whereabouts is held for ransom by Jack himself, often used as a bait to taunt Chuck mercilessly. It didn't help that Chuck had been obsessing over finding the truth over the mysterious woman who he had run into visiting Bart's grave a few months prior. The younger Bass spends entire days trying to track down his long lost mother while Jack looms in the background trying to woo Bass Industry's board of directors.

The whole situation makes her sick to her stomach. Blair tries her best to help him because it's his _mother_. And she knows how much he has yearned for some sort of connection to the woman who gave birth to him.

He told her once how when he was younger he use to conjure up this image of her, beautiful, elegant, the only woman who could warm Bart Bass's stone cold heart. How he used to fantasize what it would have been like if she lived, how un-fucked up everything would be. So the fact that she's still walking this earth means the world to him. It had the potential to change… _everything_.

Blair knows he's getting his hopes up way too high and that from that height it'll all just come tumbling down harder and faster, but the way his eyes light up with the possibilities, she doesn't dare try to pull him down to earth. The only thing left for her to do is to spend equally long amounts of time awake in the dead of night accompanying his quest to unlock the whereabouts of the elusive Evelyn Bass.

Jack is well aware of all of this and when wooing the board proves unsuccessful, thanks to the careful defense tactics on Lily's part, he decides to switch targets.

While Chuck has indeed cashed out his shares to Bass Industry, his name remains on the deed to many of the company's key enterprises. Not to mention the fact that Lily is certainly holding his seat empty for his eventually reclamation as the head of Bass Industry. From what he's gathered, Jack's best bet was to aim for Chuck, as he realized he should have done in the beginning. Get the deed to all those small, but essential, subsidiary businesses and the rest of Bass Industry would follow. It's a more indirect approach, but seeing as how many bridges have already been burnt, Jack doesn't have much left to go off on.

It's another Monday and Jack chooses that day to make his move. He makes his way through the brightly lit lobby of the Empire hotel, Chuck's newest acquisition, and marches past security and Chuck's assistant. He throws the doors open and comes face to face with his beloved nephew.

"Hey there, kid. Miss me much?"

Chuck was in the middle of some paperwork, but he quickly puts the papers down to narrow his eyes at his new guest.

"What do you want now, Jack? I heard from Lily about your pathetic attempts to sweet-talk the board. Have you realized by now that you can't flatter them as easily as those cheap hookers of yours?"

Jack laughs. "Are you referring to the ones you recommended me? By the way, Candy says 'hi'. Naw… my sights are set on a different sort of girl now… A brunette with a sharp tongue comes to mind. How is our lovely Blair anyways?"

"You stay the hell away from Blair."

"Maybe you should tell _her_ to stay away from _me_. We had quite a fun time reminiscing over New Years past the other day…"

"Is there a reason for this visit?"

"… Actually, I am here to discuss… your mother. I'd like to propose a deal… Are you interested?"

Chuck tries to keep his face cold and unaffected, but doesn't quite succeed. Despite hiring various PIs he has yet to uncover anything about her whereabouts. Wherever Jack hid her, he hid her good. A part of Chuck knows this is probably a trap, Jack is dangling this little hope only to later yank it away, but it doesn't stop him for saying what he's about to say next.

"Where is she? What do you want?"

Jack smiles a genuinely wicked smile. Chuck doesn't fail to meet his expectations.

"I'm taking that as you're interested then?"

"Yes, so get on with it!"

"I want the deed to the Palace and a few other little hotels and properties you own on this little list of mine."

Chuck snatches the piece of paper from Jack's outstretch hand and quickly runs his eyes down the list.

"These are all Bass Industry subsidiaries."

"Huh! How about that?"

"So you think if you get these then eventually you'll manage to somehow get your hands on the parent company? A little… convoluted don't you think?"

"Don't you worry about me, kiddo. How about you just hand that deed over and I'll give you this…"

Jack reaches into his pockets and reveals a card in his hand. It's one of those hotel room key cards, but Chuck doesn't recognize from where. He reaches for it, but Jack sadistically pulls out of reach. Chuck narrows his eyes in annoyance. He's done playing the cat and mouse game with his depraved uncle.

"How do I even know it's real? That you're not just playing me?"

"You don't."

"And I'm supposed to hand over the deed to some _very_ expensive real estate based on what now?"

"Faith. Hope. The only chance you're ever going to get to find your mother."

Chuck clenches his jaws tight. Business acumen and a little boy's desperate yearning for a mother war over one another.

"How about you think about it… and I'll drop on by tomorrow."

Before Jack leaves he places a small key with an elaborate engraving for the letter 'E' on Chuck's desk. It's the missing key he's been looking for to open up the matching locket he found left on his father's grave. He withdraws said necklace from his desk drawer and tries the key. The lock clicks opens and Chuck lets out a breath he didn't know he was holding. He opens the locket to reveal a dried pink rose, a photo of his mother when she was young that he's seen before and an engraving on the locket which reads:

_To Evelyn, I'll never stop loving you._

The color of the flower might be off, but everything else seems authentic. Chuck slumps back in his chair and rubs his temples. Jack Bass certainly knows how to pitch a deal in his favor.

**A/N**: Sorry for the really short updates, but I felt like this was a good place to cut off. This series will be more like a long oneshot than an actual series since I wanted to get this out before new episodes air and my whole take on the Jack Bass and Chuck's mom thing get blown completely out of the water. Anyways, enjoy!


	3. Chapter 3

**Title:** The Long Con  
**Author:** fading_tales  
**Pairing:** Chuck/Blair, Jack  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Spoilers:** WARNING! Spoilers for the upcoming episodes that haven't aired yet!  
**Summary:** All it takes a little misguided hope, expertly placed, to bring down an empire. It's what Jack Bass does best. Based on the latest spoilers for S3, takes place after 3x12 (The Debarted).

**III.**

Blair doesn't like what she hears at all. Any deal with Jack Bass might as well be a deal with the devil. She's not entirely convinced that the two are not synonymous.

"I don't trust him," Blair states bluntly.

"I don't either… but –"

"But what? This won't end well. You know that don't you?"

She needs to know that he's still maintain a bit of sanity since she's sure she's completely losing any semblance of that trait. That's what Jack Bass does to you. He turns your world upside down and makes you do funny things you wouldn't otherwise do.

---

She shows up at his office the next day to find him gathering up the paperwork for the Palace. Jack's already there, making himself at home.

"Hey there, Blair. You came just in time," Jack greets.

"Chuck, what are you doing?"

"Blair, we've talked about this."

"Yes, and last time I checked I believe we came to the conclusion that this is _Jack_ we're dealing with. Are you really going to trust _him_?" Blair points an accusatory finger towards the aforementioned elder Bass.

"He will if he ever wants to find the not so much late Mrs. Bass," Jack injects. Turning to Chuck from where he's precariously perched on the arm of the sofa, he cruelly taunts. "Evelyn is just dying to meet you."

It's exactly the right thing to say and Chuck hastens to seal the deal with the devil.

"Chuck! Do you really think this is a good idea?"

"It's my _mother_, Blair."

"Really, Blair. Chuck knows what he's doing," Jack adds.

If looks could kill, Jack should be writhing on the floor from the glare Blair shoots at him.

"Chuck, please. Just think about this! You're making a mistake!"

"Don't tell me what I can or cannot do!"

Emotions are running high and everyone's on edge.

"I'm trying to look out for you!"

"I don't need you to look out for me! I'm fine on my own!"

"Chuck!"

She takes the papers away from him in efforts to stop him from single-handedly giving over all of his hard work to the weasel that is Jack Bass. Her good intentions are met with a glare. What was it that people say about paths to hell and good intentions?

"I've said it once before, so I'll say it slowly this time around since you didn't seem to get it the first time. Stop. Playing. The. Wife. I don't need you telling me what to do!"

It's harsh, even for him and his words are met with a resounding slap across the face.

"You know what? You don't have to worry about that anymore. We're done, Chuck Bass. Done!"

The slap hurts, but not as much as it hurts to watch her walk away. Blair Waldorf certainly knows how to make a dramatic exit.

Jack stands in a corner watching the whole spectacle with a smile on his face that Chuck desperately wants to tear off.

"Good work there, nephew."

Jack places a hand on his shoulder in mock camaraderie and Chuck responds by violently shrugging it off.

"Here!" Chuck shoves a leather dossier at his nefarious uncle, "That's all of it. Now tell me where she is."

If Jack's smile could get any brighter it would probably outshine the sun. Victory never tasted so sweet. Finally, Bass Industry, as it should, will be his. And all he had to do was dangle some hope for maternal affection in front of a desperate lonely boy. He should've thought of this scheme sooner. All it took was a good actress and a few well planted bread crumbs. When someone is so desperate all it takes is a bit of hope and imagination will do the rest. Jack knows this best and Chuck doesn't disappoint.

Jack goes home, or at least to his hotel room, and pours himself a victory glass of scotch. He sips the drink and tenderly caresses the worn leather of the dossier holding the key to the future of Bass Industry. Jack has big plans and bigger hearts to break. He gives new reasons to call this day of the week Bloody Monday.

**A/N:** Gah! Angst! I always somehow end up writing at least ONE angsty CB scene. Sorry for the downer ending. Next update will be soon, I promise! =)


	4. Chapter 4

**Title:** The Long Con  
**Author:** fading_tales  
**Pairing:** Chuck/Blair, Jack  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Spoilers:** WARNING! Spoilers for the upcoming episodes that haven't aired yet!  
**Summary:** All it takes a little misguided hope, expertly placed, to bring down an empire. It's what Jack Bass does best. Based on the latest spoilers for S3, takes place after 3x12 (The Debarted).

**IV.**

It's only been a few days since they "broke up", but he already misses her terribly. When he opens the door to his suite to find her sitting there on the couch, it's like being about to breath again after staying underwater for far too long. She opens her mouth to say something, but he never hears what she was going to say because in two seconds flat, he's crossed the gap between them and covering her mouth with his.

People don't realize this, but Blair Waldorf is actually a realist disguised as a romantic and it's Chuck Bass who's the romantic pretending to be a realist. This is because other people don't know what he knows. They'd think she would be the one crushed and heartbroken if it all ended. The truth is he knows that while Blair might cry for a few days, eventually she'll gather up the pieces and move on. It's him who'll be living out the rest of his life broken, shattered, and completely unable to go on without her.

So, he kisses her as if he could make up the seconds, minutes and hours lost by kissing them away. He kisses her as if he could make the image of her walking away disappear from memory. He makes up more reasons and excuses to keep on kissing her forever.

They eventually come up for air and he's feeling satisfied by the way her lips look swollen and lightly bruised.

"What was that for? Not that I'm complaining," she says with a coy smile.

"You should stop hanging out with those Tisch kids… you're becoming too good of an actress," he states his eyes not leaving her lips. "And that slap really hurt you know." The memory makes him rub his jaw instinctively.

She laughs. "I had to make it look real so Jack wouldn't be suspicious. Besides… I thought you liked it rough."

"Next time, don't be so convincing," he leans in for another kiss.

"Come on…" She playfully takes hold of his tie and leads him into his (their) bedroom, "I'll make it up to you."

The rest of the evening is spent amongst silk sheets and down feather pillows. If anyone is looking for heaven on earth, he thinks he just found it.

---

"I'm going to meet her tomorrow," he says in a low voice.

Blair scoots closer to him, taking his hand into her own.

"... I'm scared," she answers.

He laughs. "Why are _you_ scared? Shouldn't that be my line?"

"I'm scared for _you_. I'll be the one to be scared and you just be the brave one, ok?"

She thinks that if she takes up all the fear into herself, he'll be left with nothing. As if there's some fixed quota of fear in the world and she can take it all upon herself.

"It doesn't work that way…"

He brings her hand to his lips and places a kiss on her knuckles.

"It's going to be okay. As long as you're here with me."

She smiles a sad smile at his bravado, hoping irrationally that her theory is working.

---

He meets her on a cloudy, grey winter day. The sky matches the turmoil he's feeling. It's surreal and bizarre and he feels like he's about to throw up the nonexistent breakfast he had this morning. They talk over coffee that is left untouched for the entirety of the meeting. She tells him how much she misses him, how she hadn't wanted to leave him. She paints Bart Bass, his father, as a cruel and unyielding man that forced her away. He accepts it easily because he needs to believe that she had not left him, abandoned him of her own volition. She quickly reassures him of her love.

She was as perfect as he had pictured her. Too perfect.

Thinking back on the woman claiming to be Evelyn Bass, he has to give her credit. She was a phenomenal actress. It's ironic since that was her fatal flaw. Jack had overestimated Chuck's sense of fantasy. He concocted too ideal of a character, hoping to prey on Chuck's fantasies of an elegant, wonderful, flawless mother that had been ripped away from her child. He forgot that Chuck Bass was a cynic. If something was too good to be true, it usually is.

His suspicions are confirmed when he sent someone to follow "Evelyn Bass." It's laughable how soon he discovered her true identity after all of his trouble to find her. The truth was that Chuck hadn't been able to find Evelyn Bass before because she never existed. Now that one has sprouted up to meet Jack's twisted scheme, the paper trail was easy to uncover.

Blair's worried that despite all their planning, Chuck took too much risk. Got too hurt to stand up and retaliate. She saw this coming, but she still couldn't figure out how to deal with the aftermath. He's too silent, too quiet. She can't figure out if he's too damaged, if losing his mother for the second time was too harsh a blow.

"She's really dead isn't she?"

It's the first thing he said since receiving the devastating report on the actress who played Evelyn Bass.

"Chuck…"

"I'm alright."

He's not and he knows he's not fooling anybody, least of all her.

"We'll make him pay for this. I'll make sure of it."

The determination behind her threat brings a smile to his face. There's a silver lining to this dark cloud after all.

**A/N:** Was anyone fooled by the CB breakup in the last chapter? Anyone? No? I tried to add a bit of a surprise element and make it a bit twist-y… but sorry if it came out only a little swirl-y for you. Haha. Anyways, there's just one more chapter to go to wrap it all up. Stay tuned!


	5. Chapter 5

**Title:** The Long Con  
**Author:** fading_tales  
**Pairing:** Chuck/Blair, Jack  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Spoilers:** WARNING! Spoilers for the upcoming episodes that haven't aired yet!  
**Summary:** All it takes a little misguided hope, expertly placed, to bring down an empire. It's what Jack Bass does best. Based on the latest spoilers for S3, takes place after 3x12 (The Debarted).

**V.**

Jack Bass feels like he's walking on air. All plans have come to fruitation and nothing can stop him now. So even though news that "Evelyn Bass's" true identity has been revealed to be all but a hoax, he doesn't bat an eye. The sight of a miffed Chuck Bass waiting for him in the lobby of the Empire hotel right before he's about to meet with the board of directors to finalize the official transfer of controlling power of Bass Industries? He chalks it up to a minor inconvenience. He's invincible, nothing can touch him.

Jack forgets that hubris is a crime punishable by the gods. And Jack is about to commit a few crimes, whether he knows it or not.

"Chucky boy. Came to offer me congratulations?"

"You lied to me."

"Now is that really so surprising?"

"No… but the cops coming to haul you away will be."

As if on cue, outside the hotel the sounds of sirens ring through the streets.

"What is this, Chuck? Some shenanigans conjured up in your sad little attempt to get back at me? Don't you get it? It's too late. I already have what I wanted," Jack emphasizes his meaning by holding up the leather dossier with the valuable Bass Industry deeds.

"Oh Jack… You should really learn to not count your chickens before they hatch," Blair pipes in condescendingly.

"What are _you_ doing here?" Jack bites out.

Just Chuck, he can handle. But if Blair Waldorf is in the picture, Jack Bass needs to start rethinking his situation.

"I'm just here to enjoy the show. Oh, and to move this little drama along, you might want to take a closer look at those precious deeds of yours."

Jack hurried opened the leather dossier and examined the papers he had arrogantly neglected to inspect before, too confident in his "flawless" plan.

"What the hell is this suppose to mean?!"

"It means… that you got played," Chuck answers.

"This is the _deed_!"

"No… it's more like… a forgery. Kind of like that liquor license you tried to set me up with."

"You must be slipping, Jack. We learned that trick from you," Blair chirps in.

Soon the sound of sirens halt in front of the hotel building, uniformed officers quickly join their little intimate circle.

"Is this him?" one of the men in blue asks Chuck.

"Yes."

"Jack Bass. You are under arrest for fraud and attempted robbery."

"Not to mention breaking and entering as well as trespassing," Blair adds. "I have the restraining order to prove it."

The officers proceed to cuff Jack and read him his rights.

"You've got to be kidding me. This is ridiculous. These are _juvenile_ crimes."

"A crime is a crime, Jack. Besides… it's more about the humiliation anyways," Chuck says with a smirk. "There's a lovely crowd of reputable press just waiting outside to get a good mug shot photo of you for the papers."

"Make sure they get your good side," Blair calls out as the police drag out one Jack Bass.

The sight of Jack being manhandled into the police vehicle and the buzzing mob of reporters brings a smile to her face that cannot be removed. She finds reason to like Mondays again.

---

Friday afternoon Chuck finds himself in an aircraft hangar, awaiting the take off of a private jet.

"Came to see me off? How sweet," Jack says condescendingly.

"Just making sure you board the plane. I knew you would have gotten your lawyers to drop the charges."

"I underestimated you, nephew. I'll give you that. But if you think that little prank of yours was enough to put me away for good, you have another thing coming."

"It might have not been enough to put you in jail, but it sure as hell made you lose all credibility with the board. Don't even _think_ about Bass Industries. Let's see you try anything now that you're going to be blackballed in every single credible firm in the industry. "

"It's not over, kid. If I can't have Bass Industries, then no one else will. I'll make sure it burns to the ground."

"Do you know what the funny thing about all of this is? I _wanted_ to believe you. I really did."

"I know. That's why I did it," Jack states simply. He's smiling that infuriating smile of his that makes Chuck's blood boils.

"I would've given you the real deeds if she was actually alive. I would've given you _all_ of Bass Industry on a silver fucking platter if there was a chance that my mother was really still alive."

He's hoping that despite it all, Jack might surprise him and reveal that he still holds the key to his mother. That somewhere out there Evelyn Bass was still breathing, still among one of the living. That Chuck Bass isn't just some sad orphaned cliché billionaire. The spot was reserved for Bruce Wayne and other fictional super heroes because god knows Chuck is more villain than hero.

"Kid, if Evelyn was really alive… I wouldn't need Bass Industry," Jack states solemnly.

"What do you mean?"

"It's nothing. Sorry to get your hopes up, but your mother's dead so get over it," Jack states bluntly. He puts on his sunglasses and picks up his suitcase. "I'll see you around."

Chuck leaves the hangar wondering whether or not Jack's last words were a threat or a simple good-bye.

---

Two months later it's Chuck's birthday. Blair, Serena and Nate throw him a surprise party because they knew he wouldn't do anything on his own. Despite the bitter reminder that he's still mother-less in spite of everything, his ninetieth birthday passes by without him drowning himself in alcohol or drugs. He spends it with his surrogate family and for once in his life, on this particular day, Chuck Bass is happy to be alive.

On the other side of the world, Jack Bass lays down pink roses on an unmarked grave. Bart never did get the color of her favorite flowers right. He was a hypocrite when he told Chuck to just get over it. _He_ never did. He shoves his hands into his pockets and walk away thinking of new plots to destroy Bass Industries. It's all he has left to live for.

FIN.

**A/N:** I happen to love Jack Bass… mostly because he's a jack ass. I also love Bart. Hell I love the entire Bass family. Especially any implication of what sort of relationship Bart and Jack had, maybe some Evelyn tidbits too. She was a huge presence in Bart's life and Jack seems to always have this big brother complex which implies that Evelyn was a big part of his life too. So this is my spin on it. I'm playing around with the idea of a Jack/Evelyn/Bart past!fic. Would anyone be interested in seeing that?


End file.
